Bill Paley spent his life trying to please his famous father, but found success making cigars like his grandfather

Bill Paley sits back in a leather chair in his Washington, D.C., office, a puff of smoke from his La Palina cigar dying long before it reaches the ceiling that looms high above. The room is tricked out with floor-to-ceiling bookcases, an octagonal poker table by the window overlooking the tree-lined streets of DuPont Circle and a fat, chunky CBS Radio microphone off to the side, a memento of the media empire built by his father. This is the headquarters of La Palina Cigars.

While he has only been selling cigars for two years, Paley’s boutique smokes are a revival of a brand created by his grandfather in Chicago in the 1800s. The new La Palinas—made in five varieties and counting, by four different manufacturers in as many countries—have begun to attract serious attention from the cigar community despite hitting the market with price tags of $20 and up at a time when most cigar smokers were looking for bargains. Paley’s La Palina El Diario KB, a small, dark smoke with a kick, scored 93 points in this magazine, and one of his newer creations, a small-production, truncated lancero called the Goldie sold out almost immediately.

A tall, snappy dresser of 64 years with long, silver hair and a beard, Paley has occasionally been mistaken for Jonathan Goldsmith, the actor who portrays “The Most Interesting Man in the World” in the commercials for Dos Equis. While his CV isn’t as superhuman as that of the fictional beer hero, Paley has an intriguing story all his own.

A Vietnam-war vet and college dropout, Paley served as a filmmaker for the U.S. Army, worked on propaganda for the U.S. Department of Defense, lived on a boat for several years after the war, tried the restaurant business for a time and spent some two decades as an addictions counselor, helping users battle their demons after winning a battle against addiction himself.

His full name is William S. Paley Jr., and he hails from wealth and fame. His father William S. Paley turned CBS Radio from a small radio network into a powerhouse company, founded the CBS television network and once bought the New York Yankees for the company. In addition to the microphone, Paley’s office has a tall cabinet holding three 20-inch Sony televisions that his father kept tuned to the three major networks, the entire media world, for all intents and purposes, during his day. His mother, Barbara, known as Babe, was a fashion icon. His maternal grandfather, Dr. Harvey Cushing, was a renowned brain surgeon, described by some as the father of modern neurosurgery.

Paley calls his childhood “extraordinary,” for its taste of luxury, grand homes, gourmet food and even a valet to teach him the ropes, but it was also challenging. His father was a hard-charging, competitive lion of industry who played for keeps, and being his son could be a difficult task.

“He could always see the weak point,” Paley says of his father. “As a son, nothing was right. It was very hard to live up to.”

Paley never excelled at school, which contributed to his landing in Southeast Asia. “I did a year in college, didn’t do well and I got drafted,” he says. He ended up in Vietnam, was stationed in the field filming troops, sometimes in action. “I didn’t kill anybody, I didn’t get killed,” he says. But the wartime experience had an effect on him. “I sort of had it.” He—literally—drifted for three years on a Hinckley Sou’wester yacht. “It was like a floating commune,” he says.

Paley had trouble finding himself. He tried selling yachts and dabbled in the restaurant business, and found success as an addictions counselor, helping people who went through what he went through.

“I had my own issues,” he says of addiction, saying he got clean in 1984. “Addiction is choice-less behavior. It’s the brain that’s addicted. The mind doesn’t want to be there.”

Addictions counseling was both fascinating and fulfilling to Paley, and he did it for some two decades. But after so much time spent counseling, and with his children grown and off to college, he was ready to make a change. “I had done it long enough. I had been counseling my kids, be passionate—do what you want to do.”

Paley loved smoking cigars. Before joining the cigar industry he was a twice-a-day smoker with a taste for Cubans. “My go-to smoke was a Hoyo Epi 2, and I loved the Monte 2s and Sancho Panzas. My tastes were built on Cuban tobacco.”

“Like anything in my life I got interested in, I got obsessed with it,” Paley says of cigars. When he originally thought about entering the cigar business, he first thought he had no place in the industry. “I laughed and said, ‘Who are you to make a cigar?’ ” he recalls. “But I wanted to do something I was proud of. Then it occurred to me—it was in my blood.”

The Paleys come from Brovary, a suburb of Kiev in modern-day Ukraine. In the days before the Russian Revolution, Kiev was part of the Russian Empire ruled by the tsar, and the Paley family served as his local representative, according to Bill Paley. The family was well off, with interests in lumber.

Things changed after the 1881 assassination of Tsar Alexander II. The Paley’s Jewish heritage made them a target during what followed: an intense wave of anti-Semitic rioting and scapegoating known as pogroms. The family moved to the United States, settling in Chicago.

The Paley luck turned for the worse as family patriarch Isaac Paley lost his fortune. “He had capital, played with his capital and lost his money,” says Bill Paley of his great-grandfather. That forced Isaac’s son Samuel to take a job as a lector in a local cigar factory, reading novels, newspapers and magazines to the workers. The cigar business suited Samuel, and he was later promoted to a roller and then a blender. In 1896, he went out on his own, forming Congress Cigar Co. The company’s first brand was called La Palina.

“He would roll in the window,” says Paley. “He was a small man, he had a gravelly voice—probably from the 15 cigars he smoked each day. All I have is fond memories of him.”

Eventually the cigar company grew, and in 1910 Paley moved it to Philadelphia. His son joined as vice president of advertising, and his love of radio inspired him to create “The La Palina Hour,” which brought the La Palina name to the airwaves and increased sales of the 10-cent cigars. The company bought a group of local radio stations to promote La Palina cigars, but that small acquisition turned into far, far more than anyone could have dreamt.

The elder William S. Paley loved radio a lot more than he loved cigars. Congress Cigar Co. went away after Samuel retired in 1926. The La Palina brand was sold, eventually becoming a mass-market brand, and ultimately was owned by Altadis U.S.A. Inc. For the Paleys, that small group of radio stations grew into what became known as the Tiffany Network. CBS Radio begat CBS Television, and at one time in the early 1960s Paley’s CBS had 14 of the top 15 shows in prime-time television, and CBS’s news division became the world standard under his watch. William S. Paley became a rich and powerful man.

Among the trappings of the Paley fortune was the Lightbourne House, a family retreat he and Babe built in Lyford Cay, a gated community in the Bahamas not far from the capital city of Nassau. Babe, a renowned designer, actually decorated the house, to scale, in a warehouse near her home in Long Island and had everything shipped down to the Bahamas, to make it just so.

After the death of his father in 1990 (his mother had died in 1978) Paley inherited Lightbourne House and visited the Bahamas frequently. There he met the Garzaroli family, which makes Graycliff cigars in Nassau. Paley was originally looking for a signature cigar for the Lightbourne House, which he had fashioned into a bed and breakfast.

Paley loved cigars, but lacked experience in the industry and turned to others for advice. He went to Michael Herklots, who ran New York City’s Davidoff shop on Madison Avenue at the time, asking his advice over lunch at New York’s ‘21’ Club. “I said, ‘I need you to tell me what’s wrong with the cigar,’—and he did. And I tweaked it.”

Paley set out to commercialize his new cigars. He bought back the name from Altadis. (He says he spent $5,000 on the brand name, which at the time was defunct.) He worked with a designer, studied the old imagery and took an engraving of his grandmother and turned it into the image seen on his new cigar bands. In 2010, he was ready, and Paley unveiled his first La Palinas at the International Premium Cigar & Pipe Retailers trade show. Each of the cigars were made in the Bahamas by Graycliff Cigar Co., and each paid a form of tribute to his family. The La Palina 1896 was a limited-edition, named for the year his grand-father started making cigars, and each size in the La Palina Family Series was named after a member of his family. The least expensive has a suggested retail price of $18, the priciest sells for $23.

On paper, it was a lousy time to try and sell a $20 cigar, but La Palinas drew some interest, finding homes in high-end shops such as Davidoff. “He was very adamant about starting high-end, starting limited,” says Herklots, now with Nat Sherman. “When you dig into the Paley story, it makes sense.”

Paley admits he began in a way that runs contrary to most cigar brands. “I started backwards, with the super-premium first. I knew I would be pushing uphill.” Right away, he reasoned he needed a less expensive version. He followed up in 2011 with the release of La Palina El Diario, turning to Alan Rubin of Alec Bradley Cigar Co. to help him make a less pricey blend rolled in Honduras at the Raices Cubanas cigar factory. El Diarios, made entirely of Central American tobaccos, have suggested retail prices about half that of the early La Palinas, right around $10 per cigar. The blend resulted in the highest-scoring La Palina to date, the 4 1/4 by 40 KB, which scored 93 points in the June issue of Cigar Aficionado.

“KB” stands for “Kill Bill,” because the prototype of the cigar knocked Paley on his rear. “I wasn’t able to finish smoking the first prototype,” he said soon after the launch.

With its far more reasonable price point, El Diario brought the La Palina brand into many more smoke shops. Paley expanded further this past year, adding two more regular production brands: La Palina Maduro, also made in Honduras by Raices Cubanas, and the La Palina Classic, made in the Dominican Republic by PDR Cigar Factory.

He also created a limited-edition smoke made in Miami at El Titan de Bronze, a small cigar factory on Calle Ocho in the heart of Little Havana. The cigar, called the La Palina Collection Goldie Laguito No. 2, is made entirely by one person, Maria Sierra, who has been making cigars for more than three decades, most of them spent within Cuba’s legendary El Laguito Factory.“She rolls 100 cigars a day. It took her 100 days to roll this [run],” says Paley, describing the 1,000 boxes, each containing 10 Goldies. He lauds Sierra’s cigarmaking skills, but all the evidence you need is in looking at one of her creations. The Goldies are stunning, slim smokes, with specialized flag tips called fans by some—the little tab of extra tobacco adorning the head begins ultra slim and fans out a bit.

Paley describes the Goldie as a tribute to women working in the cigar industry. The smoke is named after a woman (his paternal grandmother, Sam’s wife), made by a woman (Sierra) in a factory run by a woman (Sandy Cobas) and sold by a woman—Courtney Smith, the national sales director for La Palina cigars.

Paley wants to make more limited-edition variations of the Goldie, the first of which sold out to retailers in two weeks. And he wants Sierra to roll them. “I’ve got her basically under contract for the rest of her career,” he says.

Paley is quite comfortable following his own path in the cigar business. He says he doesn’t want to be tied to one country or one blender, and he knows he needs help making his cigars. “I don’t have the ability to be a blender myself,” he says quite frankly. Describing the La Palina house style, he promotes “smoothness and flavor,” saying “It has to be absent of bitterness.”

He doesn’t quite grasp the tasting note concept, doesn’t taste the hints of coffee bean or the wisp of leather others get when they smoke cigars. He prefers to find harmonies in his cigars. “A cigar to me is like a piece of music. It can have a lot of elements, it can be orchestral.”

Sitting back in that leather chair in his D.C. office, he takes another puff of his smoke. On the table in front of him, on a stack of books of art, lies a wooden sampler box of the original La Palina cigar brand from the 1920s. It was a box designed for traveling salesmen, with slots for each of the sizes. The box has been loaded with current La Palinas, the modern-day cigars far larger than the compartments made for their early 1900s counterparts.

“I don’t think I had ever done something that made my family proud,” Paley says. “Starting the cigar business allowed me to—rather than living up to what my father built, and all his expectations—to live up to my grandfather.”

He holds the La Palina in his hand. “I think my father could take a lot of pride in this. I’m honoring his father. This just feels right.”

Photos/Timothy Devine

Paley's office in Washington D.C. is sprinkled with wood and leather and adorned with personal mementos, including some from his father's run at CBS.